(1) Field of the Invention
The present invention relates to cocoa extracts having a reduced particle size, and to products such as foods, dietary supplements, and pharmaceuticals containing the reduced particle size cocoa extracts or additives containing the reduced particle size cocoa extracts.
(2) Description of Related Art
Polyphenolic compounds are bioactive substances that are derived from plant materials. They are closely associated with the sensory and nutritional quality of products derived from these plant materials. Many plant polyphenols have an antioxidant activity and numerous health benefits. Consumption of cocoa polyphenols (CPs) in cocoa products provides significant health benefits. Cocoa polyphenols have been shown to have beneficial effects on the processes believed to be involved in the development of atherosclerosis and cardiovascular disease. Cocoa polyphenols inhibit LDL oxidation, enhance nitric oxide/nitric oxide synthase (NO/NOS) activity, and inhibit cyclo-oxygenase (COX) and lipoxygenase (LOX) activity; these effects are reported in WO 97/36497 published Oct. 9, 1997. Cocoa polyphenols can also be used to treat or prevent conditions which are known to be affected by the administration of non-steroidal anti-inflammatory drugs, for example, aspirin.
The term “cocoa polyphenols” refers to the polyphenolic compounds, including proanthocyanidins, more particularly procyanidins, present in cocoa beans, cocoa nibs, and most cocoa ingredients prepared from cocoa beans or cocoa nibs. The term “procyanidin” refers to naturally occurring or synthetically derived oligomers of catechin and/or epicatechin. Any reference to “cocoa polyphenols” should be understood to include the flavan-3-ol monomers catechin and epicatechin. The monomers include (+)-catechin and (−)-epicatechin and their respective epimers (e.g., (+)-epicatechin and (−)-catechin) and derivatives thereof. The monomers have the formula “A” and the oligomers have the formula “An” where n in an integer from 2 to 18 and higher. “A” has the formula:
where R is 3-(α)-OH, 3-(β)-OH, 3-(α)-O-saccharide, 3-(β)-O-saccharide, 3-(α)—O—C(O)—R1, or 3-(β)—O—C(O)—R1;where bonding between adjacent monomers takes place at positions 4 and 6 or 4 and 8;where a bond to a monomer in position 4 has alpha or beta stereochemistry;where X, Y, and Z are selected from the group consisting of A, hydrogen, and a saccharide moiety, with the proviso that as to at least one terminal monomer, bonding of the adjacent monomer thereto is at position 4 and optionally Y═Z=hydrogen; andwhere the saccharide moiety is a mono- or di-saccharide moiety which may be optionally substituted with a phenolic moiety;where R1 may be an aryl or heteroaryl moiety optionally substituted with at least one hydroxy group; andsalts, derivatives, and oxidation products thereof. Advantageously, the saccharide moiety is derived from the group consisting of glucose, xylose, rhamnose, and arabinose. The saccharide moiety and any or all of R, X, Y, and Z may optionally be substituted at any position with a phenolic moiety via an ester bond. The phenolic moiety is selected from the group consisting of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoic, and sinapic acids.
Cocoa polyphenol extracts, particularly epicatechin, catechin, and procyanidin extracts, have recently been shown to possess significant biological utility. Thus, the consumption of cocoa products having a high cocoa polyphenol content may provide significant health benefits.
Cocoa polyphenol extracts, or compounds further separated therefrom, were initially prepared on a laboratory scale. See U.S. Pat. No. 5,554,645 (Romanczyk et al.) issued Sep. 10, 1996. Solid compositions and liquid preparations containing the cocoa extracts are disclosed in the '645 patent.
Underfermented and unfermented raw cocoa materials contain substantial amounts of cocoa polyphenols compared to fermented cocoa materials. Fermentation and drying bring about complex changes in the cocoa bean, most notably the formation of the components required for the development of the characteristic flavor and color of cocoa. Fermentation, however, also significantly decreases the concentrations of the polyphenolic compounds in the fermented cocoa beans relative to the concentrations of polyphenolic compounds in the unfermented or underfermented cocoa beans. Traditional cocoa bean processing, including such steps as roasting or defatting of the cocoa beans, also reduces the cocoa polyphenol concentration in the cocoa powder or chocolate liquors produced thereby. Moreover, these processes reduce the concentrations of higher oligomeric polyphenols (i.e., oligomers 5-12) more rapidly than the lower oligomers (i.e., oligomers 2-4).
Cocoa extracts containing polyphenols can also be prepared by solvent extracting partially or fully defatted cocoa solids prepared from unfermented and/or underfermented cocoa beans or cocoa nibs. See U.S. Pat. No. 6,015,913 (Kealey et al.) issued Jan. 18, 2000 and U.S. Pat. No. 6,312,753 (Kealey et al.) issued Nov. 6, 2001, the disclosures of which are incorporated herein by reference.
A process for selectively extracting tetramers, pentamers, and higher molecular weight oligomers and monomers and dimers from partially defatted cocoa solids is disclosed in U.S. Pat. No. 6,627,232 (Hammerstone et al.) issued Sep. 30, 2003, the disclosure of which is incorporated herein by reference.
A process for selectively extracting procyanidins from an aqueous mixture of cocoa polyphenols is also disclosed in U.S. 2007-0078261-A1 (Robbins, et al.) published Apr. 5, 2007, the disclosure of which is incorporated herein by reference.
A process for preventing the loss of cocoa polyphenols during the processing of partially defatted or fully defatted cocoa solids into foods or food supplements involves pre-treating the cocoa solids with about 9% to about 90% by weight of sterol and/or stanol esters which are liquids at about 80° C. or less or by pre-treating the cocoa solids with about 0.05% to about 5% by weight of a lecithin. See U.S. 2005-0069625-A1 (Chimel et al.) published Mar. 31, 2005, the disclosure of which is incorporated herein by reference.